Pyridine → Carbonic acid (4-nitrophenyl)ester (4-pentylphenyl) ester

HRID 618297Notes

Reaction equation

HRID 618297 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>C(Cl)Cl>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([O:12][C:20](=[O:21])[O:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 269754-PentylphenolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 54126542Carbonic acid (4-nitrophenyl)ester (4-pentylphenyl) esterYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-pentylphenol (20.1 g, 0.13 mol) and pyridine (10 ml, 0.13 mol) in 300 ml of methylene chloride was added under nitrogen dropwise over 45 minutes to a solution of 4-nitrophenyl chloroformate (25.28 g, 0.13 mol) in 200 ml of methylene chloride at room temperature. After the addition, the reaction was stirred overnight at room temperature. The reaction was extracted one time with 1N HCl, four times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 36.97 g of a yellow crytstalline solid. Purification of the solid on 450 g of silica gel (230-400 mesh) using 50-60% CH2Cl2 -hexane as the eluent gave 11.58 g (28%) of the title compound as a yellow crystalline solid, mp 67-69° C.

Workup

  1. additionAfter the addition
  2. extractionThe reaction was extracted one time with 1N HCl, four times with saturated Na2CO3
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customto give 36.97 g of a yellow crytstalline solid
  6. customPurification of the solid on 450 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-aa8506b03d6a4dd498eb5ec3211bcb77
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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